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My issue was specific. XenForo features automatic gzip as an application-level config option. If you are having this issue, make sure that your application does not also gzip before it reaches your server. https://xenforo.com/help/config-php-options/


It's a bug in Apache where it doesn't handle Etags properly for gzipped contents. Can be resolved by either turning off gzip (as you have noticed - but with the performance hit that entails) or turning off ETags (and depending on Last-Modified header for 304s - so no real loss). I prefer to turn off ETags. There is also an alternative option ...


you're doing proxy_pass, that's the problem. serve those files from server itself, i.e. using "root /some/path" directive, and everything should work.

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